Toluene → Methyl 5-bromopyridine-2-carboxylate

HRID 1526622Notes

Reaction equation

HRID 1526622 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[C:11]1(C)C=CC=CC=1.[Si](C=[N+]=[N-])(C)(C)C>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 167693Trimethylsilyldiazomethane2×HCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 7016458Methyl 5-bromopyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-bromopicolinic acid (2.0 g, 9.94 mmol) in MeOH (2 ml)/toluene (20 ml) was added TMS-diazomethane (20M in diethyl ether; 5.47 ml, 10.94 mmol, Matrix Scientific) dropwise. The reaction was stirred at room temperature for 3 hours. An additional 0.2 eq (0.99 mL) of TMS-diazomethane was added and the reaction stirred for 1.5 hours. The reaction was concentrated and the brown solid was carried to next step without further work up. MS m/z [M+H]+=217.9. Calculated from C7H6BrNO2: 216.032

Workup

  1. stirringthe reaction stirred for 1.5 hours
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-8990d67ceb114d89bdc4ed47b7795b66
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

Loading…